(R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide

Base Information

• Chemical Name: (R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide
• CAS No.: 181038-52-8
• Molecular Formula: C₂₇H₄₆N₄O₅
• Molecular Weight: 506.686

Synonyms:(R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide

Chemical Property of (R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide

Chemical Property:

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Technology Process of (R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide

There total 8 articles about (R)-N¹-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N⁴-(1-ethyl-propyl)-succinamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[(1S,2R)-1-((1S,2R)-1-Benzyl-3-{(R)-2-[(1-ethyl-propylcarbamoyl)-methyl]-3,3-dimethyl-butyrylamino}-2-hydroxy-propylcarbamoyl)-2-hydroxy-propyl]-carbamic acid benzyl ester → (R)-N1-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N4-(1-ethyl-propyl)-succinamide (181038-52-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; under 760 Torr;

DOI:10.1021/jm9606608

Reference yield:

tert-butyl-succinic acid (5671-87-4) → (R)-N1-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N4-(1-ethyl-propyl)-succinamide (181038-52-8)

Guidance literature:

Multi-step reaction with 7 steps

2: 95 percent / Ac₂O / 5 h / 100 °C

3: 75 percent / pyridine / Ambient temperature

4: benzotriazol-1-yl-1,1,3,3-tetramethyluronium tetrafluoroborate, N-methylmorpholine / dimethylformamide

5: 4N HCl/dioxane

6: benzotriazol-1-yl-1,1,3,3-tetramethyluronium tetrafluoroborate, N-methylmorpholine / dimethylformamide

7: H₂ / 20percent Pd(OH)2/C / methanol / 760 Torr

With 4-methyl-morpholine; pyridine; hydrogenchloride; hydrogen; acetic anhydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm9606608

Reference yield:

2-tert-butyl-butanedioic acid diethyl ester (59322-59-7) → (R)-N1-[(2R,3S)-3-((2S,3R)-2-Amino-3-hydroxy-butyrylamino)-2-hydroxy-4-phenyl-butyl]-2-tert-butyl-N4-(1-ethyl-propyl)-succinamide (181038-52-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / conc. aq. HCl / Heating

3: 95 percent / Ac₂O / 5 h / 100 °C

4: 75 percent / pyridine / Ambient temperature

5: benzotriazol-1-yl-1,1,3,3-tetramethyluronium tetrafluoroborate, N-methylmorpholine / dimethylformamide

6: 4N HCl/dioxane

7: benzotriazol-1-yl-1,1,3,3-tetramethyluronium tetrafluoroborate, N-methylmorpholine / dimethylformamide

8: H₂ / 20percent Pd(OH)2/C / methanol / 760 Torr

With 4-methyl-morpholine; pyridine; hydrogenchloride; hydrogen; acetic anhydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm9606608

upstream raw materials:

tert-butyl-succinic acid

2-tert-butyl-butanedioic acid diethyl ester

(R)-2-t-butylsuccinic anhydride

(R)-2-t-butylsuccinic acid

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